House Sitting in Red Oak Heights, Milwaukee

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Top rated Red Oak Heights house sitters

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Sitter Profile Image: Emily S.
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Emily S.
Star Sitter
from
$40
per night
5 out of 4.9 stars
26 reviews
19 repeat clients
6 years of experience
West Allis, WI, 53227

Highly recommend Emily’s services!! She made our senior dog so comfortable during her 4 day in home pet sitting. We received daily updates & pictures, and we could tell how much our dog enjoyed spending time with her! It can be nerve wracking leaving a senior dog at home, but we were never worried about our dogs care and safety while we were gone and Emily was with him.

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Ellie C.
Sitter Profile Image: Caitlin B.
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Caitlin B.
from
$60
per night
5 out of 4.8 stars
27 reviews
9 repeat clients
6 years of experience
West Allis, WI, 53227

Caitlin was absolutely phenomenal with Rigby! He went to the dog park twice while we were away getting married! I think he likes Caitlin more than us now 😉 We will def be using her again! Thanks for being the best dog sitter to our Rigby!

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Kylie S.
Sitter Profile Image: Leandrea R.
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Leandrea R.
Star Sitter
from
$60
per night
5 out of 5.0 stars
167 reviews
56 repeat clients
4 years of experience
Milwaukee, WI, 53220

Leandrea mananged to even get through trustful my shy cat. She sent many pictures and updates throughout they stay. I was even a little worried my dog and cat were going to like her more than me. Haha.

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Laura B.
Sitter Profile Image: Rachel H.
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Rachel H.
Star Sitter
from
$30
per night
5 out of 5.0 stars
90 reviews
23 repeat clients
11 years of experience
West Allis, WI, 53214

Rachel goes above and beyond every time she house sits for us. I hate leaving my pets, but I feel so much better knowing she’s there. She keeps us updated every day, and we always come home to a very happy dog and cat!

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Andrea G.
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$31
per night
5 out of 5.0 stars
15 reviews
8 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

We had Keisha stay for a 7 day sit for our dog and cat. Keisha was incredible and everything we could have ever wanted in a sitter! She sent us updates at least daily, sometimes more with pictures which is what we requested! I made an error and she was flexible with adding another day to her stay! Could not recommend her enough, we will definitely use her again in the future!!

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Jordyn
Sitter Profile Image: Jenn S.
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Jenn S.
Star Sitter
from
$60
per night
5 out of 5.0 stars
62 reviews
18 repeat clients
40 years of experience
West Allis, WI, 53227

Jenn did a great job with both of our dogs. One of our dogs is very skittish and she handled it really well. I would definitely leave them in her care again.

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Katie F.
Sitter Profile Image: Liz B.
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Liz B.
Star Sitter
from
$50
per night
5 out of 4.9 stars
35 reviews
12 repeat clients
7 years of experience
West Allis, WI, 53214

Liz was wonderful! Excellent communication. This was my first time using Rover and she made for an amazing first experience. I will definitely use her services again.

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Stacy J.
Sitter Profile Image: Joely Stella F.
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Joely Stella F.
Star Sitter
from
$33
per night
5 out of 4.9 stars
23 reviews
8 repeat clients
5 years of experience
Milwaukee, WI, 53129

Joely was fantastic with my dog and cat on two house sitting occasions so far. Treated them with love and care and communicated well and sent fun photos. My older dog had some tummy issues while I was away this last time and Joely managed it all like a pro and kept me informed every day. Highly recommend!!

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Keri A.
Sitter Profile Image: Jessica R.
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Jessica R.
from
$45
per night
5 out of 5.0 stars
12 reviews
16 years of experience
Woodland Court, Milwaukee, WI, 53220

Jessica was great with our lab! Also sent pictures and spent quality time with her! Would definitely book with her again.

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Amelia G.
Sitter Profile Image: Daniela & Michael P.
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Daniela & Michael P.
from
$65
per night
5 out of 4.9 stars
289 reviews
165 repeat clients
11 years of experience
Bay View, Milwaukee, WI, 53207

Daniela is the perfect pet sitter and can handle our great dane! Our dog was on medications while we were away and she did a great job with his extra needs. We will keep booking wjth Daniela!

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Steve C.
Sitter Profile Image: Blythe R.
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Blythe R.
Star Sitter
from
$75
per night
5 out of 5.0 stars
173 reviews
66 repeat clients
7 years of experience
Bay View, Milwaukee, WI, 53207

Blythe was amazing! I booked with her based on her endless positive reviews and was not disappointed. I have a blind senior dog who needs medication and Blythe went above and beyond to make me feel less anxious about leaving her for the first time for a long weekend. She was communicative, patient and kind—I will definitely be booking with her for my next trip.

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Megan S.
Sitter Profile Image: Serena L.
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Serena L.
from
$30
per night
5 out of 5.0 stars
5 reviews
1 repeat client
10 years of experience
Hales corners, WI, 53130

About: I have helped take care of many different dog breeds since I was little. Additionally, I worked at a dog daycare for six months, where I gained hands-on experience with dogs of all ages and temperaments. I have experience caring for both senior dogs and puppies, ensuring they receive the specialized attention they need. I’m also familiar with training basic commands, helping dogs build good manners and confidence. My background allows me to provide attentive, knowledgeable, and loving care for every pet I watch. I’m available all day on weekends and from 7 AM to 1 PM on weekdays. I can also accommodate pet care on select holidays. Whether your pet needs a quick visit, extended care, or a structured routine, I’m happy to create a schedule that works for both you and your furry friend. I prioritize safety, trust, and a comfortable environment when caring for pets. I follow established routines, provide enrichment, and ensure a stress-free space. I’m attentive to each pet’s unique needs, from feeding and exercise to companionship and basic training. Occasionally, my boyfriend may accompany me during walks or drop-in visits—he’s also great with animals and simply provides company and an extra set of helping hands when needed. Of course, this is only if the client is fully comfortable with it. My goal is always to create a secure, loving atmosphere where pets feel safe, happy, and well cared for.

Sitter Profile Image: Ashley W.
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Ashley W.
from
$45
per night
5 out of 5.0 stars
14 reviews
5 repeat clients
10 years of experience
Washington Heights, Milwaukee, WI, 53208

Ashley was GREAT! I had a last minute trip pop up this weekend and she immediately responded to help me out. She even dropped what she was doing to come meet her that night! She was super responsive while I was away, and Brooklyn is worn out tonight- which I know is because she had so much fun! Thanks again, Ashley!

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Graham B.
Sitter Profile Image: Ashley S.
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Ashley S.
from
$27
per night
5 out of 5.0 stars
7 reviews
1 repeat client
13 years of experience
West Allis, WI, 53227

Ashley was incredible! She took amazing care of my dog Jax while I was away. She kept in regular communication, sent plenty of photo updates, and made me feel completely at ease the entire time. I came home to a happy pup and even found a thoughtful little gift she left on the counter—such a sweet touch. I absolutely plan to book with her again in a few months. 10/10 highly recommend!

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Tylor W.
Sitter Profile Image: Berenice B.
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Berenice B.
Star Sitter
from
$75
per night
5 out of 4.9 stars
165 reviews
70 repeat clients
15 years of experience
Bay View, Milwaukee, WI, 53207

Berenice was an excellent sitter. My first time working with her was for an extended period of time and I came home to a clean house and happy, healthy dogs. My two pitties are not trained well on a leash and she did well walking them despite that. She left me at ease while on my trip with daily communication and pictures. We already have our next stay booked with her! Thank you Berenice! 💕

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Amy N.
Sitter Profile Image: Sarah J.
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Sarah J.
Star Sitter
from
$50
per night
5 out of 5.0 stars
279 reviews
66 repeat clients
5 years of experience
West allis, WI, 53219

Sarah was amazing!!sent updates and pictures during her stay. Came back to a clean house and happy pets! We will definitely be having her watch our girls again :)

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Justine R.
Sitter Profile Image: Katie M.
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Katie M.
Star Sitter
from
$50
per night
5 out of 5.0 stars
24 reviews
7 repeat clients
15 years of experience
Elm Grove, WI, 53122

Katie did a great job with our two dogs, one which is a senior and needs a lot of help! She sent us plenty of pics and even brought in our mail while we were away. She did an excellent job!

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Monika R.
Sitter Profile Image: Patricia N.
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Patricia N.
Star Sitter
from
$40
per night
5 out of 5.0 stars
71 reviews
19 repeat clients
30 years of experience
Franklin, WI, 53132

We loved having Pat watch our 2 fur boys. She sent pics and texts and we felt so comfortable knowing that Dill and Rocky were in great hands!!

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Linda G.
Sitter Profile Image: Stephen & Wipawee D.
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Stephen & Wipawee D.
Star Sitter
from
$95
per night
5 out of 5.0 stars
49 reviews
19 repeat clients
5 years of experience
West Allis, WI, 53227

We couldn't have asked for a better experience! Stephen and Amilie were very communicative to us about how our animals are doing. We felt very comfortable with them and they took great care of our animals! We would no doubt use their services again!

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Rebekah J.
Sitter Profile Image: Harley Z.
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Harley Z.
Star Sitter
from
$50
per night
5 out of 4.8 stars
23 reviews
8 repeat clients
12 years of experience
Muskego, WI, 53150

Harley did an amazing job watching our fur baby Zoey. She communicated with us the whole time and sent alot of pictures. We would definitely use Harley for future bookings.

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Mark S.
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Sitter Profile Image: Emily S.
Verified Enhanced Background Check
Sitter Profile Image: Emily S.
Verified Enhanced Background Check

1. Emily S.

Star Sitter
Enjoy making pets happy and loved
West Allis, WI, 53227
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 4.9 stars
26 reviews
19 repeat clients
Profile image

Highly recommend Emily’s services!! She made our senior dog so comfortable during her 4 day in home pet sitting. We received daily updates & pictures, and we could tell how much our dog enjoyed spending time with her! It can be nerve wracking leaving a senior dog at home, but we were never worried about our dogs care and safety while we were gone and Emily was with him.

Availability updated yesterday
Sitter Profile Image: Caitlin B.
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Sitter Profile Image: Caitlin B.
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2. Caitlin B.

Rover 101
Passionate animal lover
West Allis, WI, 53227
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 4.8 stars
27 reviews
9 repeat clients
Profile image

Caitlin was absolutely phenomenal with Rigby! He went to the dog park twice while we were away getting married! I think he likes Caitlin more than us now 😉 We will def be using her again! Thanks for being the best dog sitter to our Rigby!

Availability updated 5 days ago
Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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3. Leandrea R.

Rover 101
Star Sitter
your pets are my priority.
Milwaukee, WI, 53220
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 5.0 stars
167 reviews
56 repeat clients
Profile image

Leandrea mananged to even get through trustful my shy cat. She sent many pictures and updates throughout they stay. I was even a little worried my dog and cat were going to like her more than me. Haha.

Availability updated today
Sitter Profile Image: Rachel H.
Verified Background Check
Sitter Profile Image: Rachel H.
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4. Rachel H.

Star Sitter
** Mission: meet ALL the dogs **
West Allis, WI, 53214
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
90 reviews
23 repeat clients
Profile image

Rachel goes above and beyond every time she house sits for us. I hate leaving my pets, but I feel so much better knowing she’s there. She keeps us updated every day, and we always come home to a very happy dog and cat!

Availability updated 11 days ago
Sitter Profile Image: Keisha P.
Verified Enhanced Background Check
Sitter Profile Image: Keisha P.
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5. Keisha P.

Star Sitter
Your Furbabies will Love Me
Clarke Square, Milwaukee, WI, 53204
4.5 mi. away
House Sitting, Drop-In Visits
from
$31
per night
5 out of 5.0 stars
15 reviews
8 repeat clients
Profile image

We had Keisha stay for a 7 day sit for our dog and cat. Keisha was incredible and everything we could have ever wanted in a sitter! She sent us updates at least daily, sometimes more with pictures which is what we requested! I made an error and she was flexible with adding another day to her stay! Could not recommend her enough, we will definitely use her again in the future!!

Availability updated yesterday
Sitter Profile Image: Jenn S.
Verified Enhanced Background Check
Sitter Profile Image: Jenn S.
Verified Enhanced Background Check

6. Jenn S.

Star Sitter
Dedicated & Reliable 🐕🐈🦜🐟
West Allis, WI, 53227
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
62 reviews
18 repeat clients
Profile image

Jenn did a great job with both of our dogs. One of our dogs is very skittish and she handled it really well. I would definitely leave them in her care again.

Availability updated today
Sitter Profile Image: Liz B.
Verified Enhanced Background Check
Sitter Profile Image: Liz B.
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7. Liz B.

Rover 101
Star Sitter
Senior pet lover and expert!
West Allis, WI, 53214
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 4.9 stars
35 reviews
12 repeat clients
Profile image

Liz was wonderful! Excellent communication. This was my first time using Rover and she made for an amazing first experience. I will definitely use her services again.

Availability updated yesterday
Sitter Profile Image: Joely Stella F.
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Sitter Profile Image: Joely Stella F.
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8. Joely Stella F.

Star Sitter
An animal lover who loves pets!
Milwaukee, WI, 53129
1.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$33
per night
5 out of 4.9 stars
23 reviews
8 repeat clients
Profile image

Joely was fantastic with my dog and cat on two house sitting occasions so far. Treated them with love and care and communicated well and sent fun photos. My older dog had some tummy issues while I was away this last time and Joely managed it all like a pro and kept me informed every day. Highly recommend!!

Availability updated 2 days ago
Sitter Profile Image: Jessica R.
Verified Enhanced Background Check
Sitter Profile Image: Jessica R.
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9. Jessica R.

A dogs best friend🩷
Woodland Court, Milwaukee, WI, 53220
0.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
12 reviews
Profile image

Jessica was great with our lab! Also sent pictures and spent quality time with her! Would definitely book with her again.

Availability updated 11 days ago
Sitter Profile Image: Daniela & Michael P.
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Sitter Profile Image: Daniela & Michael P.
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10. Daniela & Michael P.

Rover 101
Paws Down, the Best in Town!
Bay View, Milwaukee, WI, 53207
5.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 4.9 stars
289 reviews
165 repeat clients
Profile image

Daniela is the perfect pet sitter and can handle our great dane! Our dog was on medications while we were away and she did a great job with his extra needs. We will keep booking wjth Daniela!

Availability updated 2 days ago
Sitter Profile Image: Blythe R.
Verified Background Check
Sitter Profile Image: Blythe R.
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11. Blythe R.

Star Sitter
Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
5.6 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
173 reviews
66 repeat clients
Profile image

Blythe was amazing! I booked with her based on her endless positive reviews and was not disappointed. I have a blind senior dog who needs medication and Blythe went above and beyond to make me feel less anxious about leaving her for the first time for a long weekend. She was communicative, patient and kind—I will definitely be booking with her for my next trip.

Availability updated 4 days ago
Sitter Profile Image: Serena L.
Verified Enhanced Background Check
Sitter Profile Image: Serena L.
Verified Enhanced Background Check

12. Serena L.

Trusted, Loving Care for Your Pets!
Hales corners, WI, 53130
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
5 reviews
1 repeat client

Serena is a very reliable, efficient and friendly with my dogs and cats. We have had Serena sit for our 2 dogs and 3 cats when on vacation and quick nights out. She had always gotten alone with all our animals.

Availability updated 3 days ago
Sitter Profile Image: Ashley W.
Verified Background Check
Sitter Profile Image: Ashley W.
Verified Background Check

13. Ashley W.

Active person loves active dogs
Washington Heights, Milwaukee, WI, 53208
6.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5 out of 5.0 stars
14 reviews
5 repeat clients
Profile image

Ashley was GREAT! I had a last minute trip pop up this weekend and she immediately responded to help me out. She even dropped what she was doing to come meet her that night! She was super responsive while I was away, and Brooklyn is worn out tonight- which I know is because she had so much fun! Thanks again, Ashley!

Availability updated 36 days ago
Sitter Profile Image: Ashley S.
Verified Enhanced Background Check
Sitter Profile Image: Ashley S.
Verified Enhanced Background Check

14. Ashley S.

Animal Care Professional/Lover
West Allis, WI, 53227
2.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$27
per night
5 out of 5.0 stars
7 reviews
1 repeat client
Profile image

Ashley was incredible! She took amazing care of my dog Jax while I was away. She kept in regular communication, sent plenty of photo updates, and made me feel completely at ease the entire time. I came home to a happy pup and even found a thoughtful little gift she left on the counter—such a sweet touch. I absolutely plan to book with her again in a few months. 10/10 highly recommend!

Availability updated 2 days ago
Sitter Profile Image: Berenice B.
Verified Enhanced Background Check
Sitter Profile Image: Berenice B.
Verified Enhanced Background Check

15. Berenice B.

Rover 101
Star Sitter
I walk to keep their tails waggin’
Bay View, Milwaukee, WI, 53207
5.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$75
per night
5 out of 4.9 stars
165 reviews
70 repeat clients
Profile image

Berenice was an excellent sitter. My first time working with her was for an extended period of time and I came home to a clean house and happy, healthy dogs. My two pitties are not trained well on a leash and she did well walking them despite that. She left me at ease while on my trip with daily communication and pictures. We already have our next stay booked with her! Thank you Berenice! 💕

Availability updated today
Sitter Profile Image: Sarah J.
Verified Enhanced Background Check
Sitter Profile Image: Sarah J.
Verified Enhanced Background Check

16. Sarah J.

Star Sitter
I’m awkward with humans.
West allis, WI, 53219
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5 out of 5.0 stars
279 reviews
66 repeat clients
Profile image

Sarah was amazing!!sent updates and pictures during her stay. Came back to a clean house and happy pets! We will definitely be having her watch our girls again :)

Availability updated today
Sitter Profile Image: Katie M.
Verified Enhanced Background Check
Sitter Profile Image: Katie M.
Verified Enhanced Background Check

17. Katie M.

Star Sitter
Happy Pets, Self-Insured Care!
Elm Grove, WI, 53122
7.5 mi. away
Boarding, House Sitting, Drop-In Visits
from
$50
per night
5 out of 5.0 stars
24 reviews
7 repeat clients
Profile image

Katie did a great job with our two dogs, one which is a senior and needs a lot of help! She sent us plenty of pics and even brought in our mail while we were away. She did an excellent job!

Availability updated 6 days ago
Sitter Profile Image: Patricia N.
Verified Enhanced Background Check
Sitter Profile Image: Patricia N.
Verified Enhanced Background Check

18. Patricia N.

Star Sitter
Love them all!
Franklin, WI, 53132
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
71 reviews
19 repeat clients
Profile image

We loved having Pat watch our 2 fur boys. She sent pics and texts and we felt so comfortable knowing that Dill and Rocky were in great hands!!

Availability updated 46 days ago
Sitter Profile Image: Stephen & Wipawee D.
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Sitter Profile Image: Stephen & Wipawee D.
Verified Enhanced Background Check

19. Stephen & Wipawee D.

Star Sitter
Pawfessional w/ Love & Care <3
West Allis, WI, 53227
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$95
per night
5 out of 5.0 stars
49 reviews
19 repeat clients
Profile image

We couldn't have asked for a better experience! Stephen and Amilie were very communicative to us about how our animals are doing. We felt very comfortable with them and they took great care of our animals! We would no doubt use their services again!

Availability updated 6 days ago
Sitter Profile Image: Harley Z.
Verified Enhanced Background Check
Sitter Profile Image: Harley Z.
Verified Enhanced Background Check

20. Harley Z.

Star Sitter
Pet whisperer here to help!
Muskego, WI, 53150
7.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 4.8 stars
23 reviews
8 repeat clients
Profile image

Harley did an amazing job watching our fur baby Zoey. She communicated with us the whole time and sent alot of pictures. We would definitely use Harley for future bookings.

Availability updated yesterday

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